14190-59-1

Basic information

• Product Name: THIAZOLE-2-CARBOXYLIC ACID
• Synonyms: 1,3-THIAZOLE-2-CARBOXYLIC ACID;RARECHEM AL BE 0750;THIAZOLE-2-CARBOXYLIC ACID;2-THIAZOLECARBOXYLIC ACID,THIAZOLE-2-CARBOXYLIC ACID;Thiazole-2-carboxylic acid ,98%;2-THIAZOLECARBOXYLIC;2-Carboxy-1,3-thiazole;thiazol-2-carboxylic acid
• CAS NO: 14190-59-1
• Molecular Formula: C4H3NO2S
• Molecular Weight: 129.14
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Thiazole series;Carboxylic Acids;Thiazoles, Isothiazoles &Benzothiazoles;Carboxylic Acids;Thiazoles, Isothiazoles & Benzothiazoles
• Mol File: 14190-59-1.mol
• Article Data: 14

Chemical Properties

• Melting Point: 91.6-93°C
• Boiling Point: 310.6 °C at 760 mmHg
• Flash Point: 141.6 °C
• Appearance: /Solid
• Density: 1.525 g/cm³
• Vapor Pressure: 0.000256mmHg at 25°C
• Refractive Index: 1.617
• Storage Temp.: ?20°C
• PKA: 2.95±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: THIAZOLE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: THIAZOLE-2-CARBOXYLIC ACID(14190-59-1)
• EPA Substance Registry System: THIAZOLE-2-CARBOXYLIC ACID(14190-59-1)

Safety Data

• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39-22
• WGK Germany: 1
• Hazardous Substances Data: 14190-59-1(Hazardous Substances Data)

Usage

Description

Thiazole-2-carboxylic acid is an organic compound that serves as a crucial raw material and intermediate in various industries, including organic synthesis, pharmaceuticals, agrochemicals, and dyestuff. It is characterized by its beige to light yellow powdery appearance.

Uses

Used in Organic Synthesis:
Thiazole-2-carboxylic acid is used as a key intermediate for the synthesis of various organic compounds, contributing to the development of new molecules with potential applications in different fields.
Used in Pharmaceutical Industry:
Thiazole-2-carboxylic acid is utilized as a building block in the development of pharmaceutical drugs, playing a significant role in the creation of novel therapeutic agents.
Used in Agrochemicals:
In the agrochemical industry, Thiazole-2-carboxylic acid is employed as a vital component in the formulation of pesticides and other agricultural chemicals, aiming to enhance crop protection and yield.
Used in Dyestuff Industry:
Thiazole-2-carboxylic acid is used as a starting material in the production of dyes, contributing to the development of a wide range of colorants for various applications, such as textiles, plastics, and printing inks.

InChI:InChI=1/C4H3NO2S/c6-4(7)3-5-1-2-8-3/h1-2H,(H,6,7)

Synthetic route

2-bromo-1,3-thiazole (3034-53-5) + carbon dioxide (124-38-9) → 1,3-thiazole-2-carboxylic acid (14190-59-1)

Conditions	Yield
Stage #1: 2-bromo-1,3-thiazole With n-butyllithium In tetrahydrofuran Stage #2: carbon dioxide	73%
Stage #1: 2-bromo-1,3-thiazole With n-butyllithium In diethyl ether; hexane at -78℃; for 0.166667h; Stage #2: carbon dioxide In diethyl ether; hexane at -78℃; for 1.16667h;	64%

1,3-thiazole (288-47-1) + carbon dioxide (124-38-9) → thiazole-5-carboxylic acid (14527-41-4) + 1,3-thiazole-2-carboxylic acid (14190-59-1)

Conditions	Yield
Stage #1: carbon dioxide With AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); potassium hydroxide In tetrahydrofuran at 20℃; under 1125.11 Torr; for 0.25h; Stage #2: 1,3-thiazole In tetrahydrofuran at 20℃; under 1125.11 Torr; for 12h; Stage #3: With hydrogenchloride In tetrahydrofuran; water regioselective reaction;	A 27% B 61%

2-bromo-1,3-thiazole (3034-53-5) + water (7732-18-5) → 1,3-thiazole-2-carboxylic acid (14190-59-1) + ETHYL 2-[N-(1'-AMINOCITRACONAMIDO)]-4-(2'-THIAZOLYL)PYRIMIDINE-5-CARBOXYLATE

Conditions	Yield
With n-butyllithium; carbon dioxide	A 57% B n/a

thiazole-2-carboxylic acid ethyl ester (14527-42-5) → 1,3-thiazole-2-carboxylic acid (14190-59-1)

Conditions	Yield
Stage #1: thiazole-2-carboxylic acid ethyl ester With potassium hydroxide; ethanol; water at 20℃; for 2h; Stage #2: With hydrogenchloride; water In ethanol	25%
With potassium hydroxide
Stage #1: thiazole-2-carboxylic acid ethyl ester With potassium hydroxide; ethanol at 120℃; for 0.5h; Stage #2: With hydrogenchloride; water In ethanol pH=4.0;
Stage #1: thiazole-2-carboxylic acid ethyl ester With potassium hydroxide; ethanol at 120℃; for 0.5h; Stage #2: With hydrogenchloride In ethanol; water pH=4.0;
Stage #1: thiazole-2-carboxylic acid ethyl ester With potassium hydroxide; ethanol; water at 20℃; for 2h; Stage #2: With hydrogenchloride; water

1,3-thiazole (288-47-1) → 1,3-thiazole-2-carboxylic acid (14190-59-1)

Conditions	Yield
With diethyl ether; phenyllithium anschliessend Behandeln mit CO2;

2-bromo-1,3-thiazole (3034-53-5) → 1,3-thiazole-2-carboxylic acid (14190-59-1)

Conditions	Yield
With n-butyllithium; diethyl ether anschliessend mit CO2;

thiocarboxamide (115-08-2) + formylchloroacetic acid ethyl ester → 1,3-thiazole-2-carboxylic acid (14190-59-1)

Conditions	Yield
beim anschliessenden Verseifen; reagirt analog mit 2-Chlor-acetessigsaeure-aethylester, 3-Chlor-laevulinsaeure-aethylester,;

C4H2NO2S(1-)*Li(1+) (1192365-76-6) → 1,3-thiazole-2-carboxylic acid (14190-59-1)

Conditions	Yield
With sulfuric acid; water

1,3-thiazole (288-47-1) + carbon dioxide (124-38-9) → 1,3-thiazole-2-carboxylic acid (14190-59-1)

Conditions	Yield
Stage #1: 1,3-thiazole With n-butyllithium In tetrahydrofuran at -60℃; for 0.166667h; Stage #2: carbon dioxide In tetrahydrofuran
Stage #1: 1,3-thiazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere;	12 g

1,3-thiazole-2-carboxylic acid (14190-59-1) + 6-aminohexanoic acid phenylamide (115012-25-4) → thiazole-2-carboxylic acid (5-phenylcarbamoyl-pentyl)-amide

Conditions	Yield
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;	94%

1,3-thiazole-2-carboxylic acid (14190-59-1) + 2-amino-phenol (95-55-6) → 2-(thiazol-2-yl)benzo[d]oxazole

Conditions	Yield
With PS-PPh3; trichloroacetonitrile In acetonitrile at 150℃; for 0.25h; microwave irradiation;	94%

1,3-thiazole-2-carboxylic acid (14190-59-1) + 1-(3-amino-2,6-difluoro-phenyl)-ethanone (99724-35-3) → thiazole-2-carboxylic acid (3-acetyl-2,4-difluoro-phenyl)-amide (746630-05-7)

Conditions	Yield
With triethylamine; HATU In tetrahydrofuran	92%

1,3-thiazole-2-carboxylic acid (14190-59-1) + 3-(8-nitroquinolin-4-yl)benzenamine → N-(3-(8-nitroquinolin-4-yl)phenyl)thiazole-2-carboxamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃;	92%

1,3-thiazole-2-carboxylic acid (14190-59-1) + ethyl potassium malonate (6148-64-7) → 3-oxo-3-thiazol-2-yl-propionic acid ethyl ester (212621-63-1)

Conditions	Yield
Stage #1: 1,3-thiazole-2-carboxylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 4h; Stage #2: ethyl potassium malonate With magnesium chloride In tetrahydrofuran at 50 - 75℃; for 20h;	91%

1,3-thiazole-2-carboxylic acid (14190-59-1) + 2-[5-amino-2-[(1r,4r)-4-(hydroxymethyl)cyclohexyl]indazol-6-yl]propan-2-ol → N-(2-((1r,4r)-4-(hydroxymethyl)cyclohexyl)-6-(2-hydroxypropan-2-yl)-2H-indazol-5-yl)thiazole-2-carboxamide

Conditions	Yield
With 2-chloro-1-methyl-pyridinium iodide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 0.5h; Inert atmosphere;	91%

1,3-thiazole-2-carboxylic acid (14190-59-1) + 1-(1-benzhydrylazetidin-3-yl)piperazine (930782-73-3) → (4-(1-benzhydrylazetidin-3-yl)piperazin-1-yl)(thiazol-2-yl)methanone (1252779-95-5)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane for 48h;	90%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane for 48h; Inert atmosphere;	90%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In water; N,N-dimethyl-formamide at 20℃; for 16h;	78%

1,3-thiazole-2-carboxylic acid (14190-59-1) + 2-Fluoroaniline (348-54-9) → N-(2-fluorophenyl)thiazole-2-carboxamide

Conditions	Yield
With pyridine; trichlorophosphate In dichloromethane at 20℃; Cooling with ice;	79%
With pyridine; trichlorophosphate In dichloromethane at 20℃; Cooling with ice;	79%

1,3-thiazole-2-carboxylic acid (14190-59-1) + 4-chlorobenzoic acid hydrazide (536-40-3) → N'-(4-chlorobenzoyl)thiazole-2-carbohydrazide

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In N,N-dimethyl-formamide at 20℃;	73%

1,3-thiazole-2-carboxylic acid (14190-59-1) + 1-(4-phenoxyphenyl)-4-(piperazin-1-yl)pyrrolidin-2-one hydrochloride → 1-(4-phenoxyphenyl)-4-(4-(1,3-thiazol-2-ylcarbonyl)piperazin-1-yl)pyrrolidin-2-one

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	71%
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 10 - 35℃;	170 mg

1,3-thiazole-2-carboxylic acid (14190-59-1) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → thiazole-2-carboxylic acid methoxy-methyl-amide (885278-18-2)

Conditions	Yield
Stage #1: 1,3-thiazole-2-carboxylic acid With 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In tetrahydrofuran at 0℃; for 0.25h; Stage #2: With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 1.5h; Stage #3: N,O-dimethylhydroxylamine*hydrochloride In tetrahydrofuran at 0 - 20℃;	70%
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide

1,3-thiazole-2-carboxylic acid (14190-59-1) + N-(2'-chloro-5'-aminobenzoyl)-4-(p-fluorobenzy)-piperidine hydrochloride (944390-13-0) → thiazole-2-carboxylic acid {4-chloro-3-[4-(4-fluoro-benzyl)-piperidine-1-carbonyl]-phenyl}-amide

Conditions	Yield
Stage #1: 1,3-thiazole-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate In acetonitrile for 0.25h; Stage #2: N-(2'-chloro-5'-aminobenzoyl)-4-(p-fluorobenzy)-piperidine hydrochloride With N-ethyl-N,N-diisopropylamine In acetonitrile for 2.25h;	69%

1,3-thiazole-2-carboxylic acid (14190-59-1) + potassium tert-butylate (865-47-4) → tert-butyl thiazole-2-carboxylate

Conditions	Yield
Stage #1: 1,3-thiazole-2-carboxylic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 23℃; for 5h; Stage #2: potassium tert-butylate In dichloromethane; N,N-dimethyl-formamide at 23℃; for 1h; Temperature;	67%
Stage #1: 1,3-thiazole-2-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 23℃; for 5h; Stage #2: potassium tert-butylate In dichloromethane at 23℃; for 1h;	67%

1,3-thiazole-2-carboxylic acid (14190-59-1) + Demethylmifepristone (104004-96-8) → N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methylthiazole-2-carboxamide

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h; Inert atmosphere;	66%

N2-phenyl-5-amino-3-methyl-2,4-thiophenecarboxamide (331959-40-1) + 1,3-thiazole-2-carboxylic acid (14190-59-1) → 3-methyl-N2-phenyl-5-(thiazole-2-carboxamido)thiophene-2,4-dicarboxamide

Conditions	Yield
Stage #1: 1,3-thiazole-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: N2-phenyl-5-amino-3-methyl-2,4-thiophenecarboxamide In N,N-dimethyl-formamide at 20℃;	66%

1,3-thiazole-2-carboxylic acid (14190-59-1) + hex-5-ynyl methanesulphonate (79496-61-0) → C10H11NO2S

Conditions	Yield
With potassium carbonate In acetonitrile at 90℃; for 0.5h; Microwave irradiation;	61%

1,3-thiazole-2-carboxylic acid (14190-59-1) + cloridrato del 2-amino-2-isobutirrilacetacetato di etile → ethyl 5-methyl-3-oxo-2-(thiazole-2-carboxamido)hexanoate (910476-37-8)

Conditions	Yield
With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃; Molecular sieve;	60%
With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃; Molecular sieve;	60%

1,3-thiazole-2-carboxylic acid (14190-59-1) + (S)-1-amino-N-(3-chloro-4-fluorophenyl)-7-fluoro-2,3-dihydro-1H-indene-4-carboxamide hydrochloride → (S)-N-(4-((3-chloro-4-fluorophenyl)carbamoyl)-7-fluoro-2,3-dihydro-1H-inden-1-yl)thiazole-2-carboxamide

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane at 0 - 20℃; for 16h;	60%

1,3-thiazole-2-carboxylic acid (14190-59-1) + 4-methylthiosemicarbazide (6610-29-3) → 4-methyl-5-(1,3-thiazol-2-yl)-4H-1,2,4-triazole-3-thiol

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; N,N-dimethyl-formamide at 20℃; Cooling with ice;	59%
Stage #1: 1,3-thiazole-2-carboxylic acid; 4-methylthiosemicarbazide With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; N,N-dimethyl-formamide at 20℃; for 12h; Stage #2: With sodium hydroxide for 0.666667h; Reflux;
Stage #1: 1,3-thiazole-2-carboxylic acid; 4-methylthiosemicarbazide With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; N,N-dimethyl-formamide at 0 - 20℃; Stage #2: With sodium hydroxide In ethyl acetate; N,N-dimethyl-formamide at 70℃;

1,3-thiazole-2-carboxylic acid (14190-59-1) + C9H17NO3*2ClH → ethyl 5-methyl-3-oxo-2-(thiazole-2-carboxamido)hexanoate (910476-37-8)

Conditions	Yield
Stage #1: C9H17NO3*2ClH With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 0.166667h; Stage #2: 1,3-thiazole-2-carboxylic acid With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	59%

1,3-thiazole-2-carboxylic acid (14190-59-1) + C9H10Cl2N2 → C13H11Cl2N3OS

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;	57%

1,3-thiazole-2-carboxylic acid (14190-59-1) + (S)-3-[3-(4-fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-piperidine (851882-63-8) → {(S)-3-[3-(4-fluoro-phenyl)-1,2,4-oxadiazol-5-yl]-piperidin-1-yl}-thiazol-2-yl-methanone

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; PS-DCC; N-ethyl-N,N-diisopropylamine In dichloromethane	55%

1,3-thiazole-2-carboxylic acid (14190-59-1) + water (7732-18-5) + zinc(II) acetate dihydrate (5970-45-6) → bis(κ2-N,O-thiazole-2-carboxylate)diaquazinc(II) (1270159-28-8)

Conditions	Yield
In water High Pressure; metal:thiazole=2:1 molar ratio, heated at 90°C for 24 h; slowly cooled overnight, crysts. washed (ethanol), dried (N2 stream, room temp.); elem. anal., single cryst. XRD, TGA;	55%

1,3-thiazole-2-carboxylic acid (14190-59-1) + 2-phenyl-1,3-benzothiazol-5-amine (43087-91-8) → N-(2-phenylbenzo[d]thiazol-5-yl)thiazole-2-carboxamide

Conditions	Yield
Stage #1: 1,3-thiazole-2-carboxylic acid With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 1.5h; Stage #2: 2-phenyl-1,3-benzothiazol-5-amine In tetrahydrofuran	55%
Stage #1: 1,3-thiazole-2-carboxylic acid With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 1.5h; Stage #2: 2-phenyl-1,3-benzothiazol-5-amine In tetrahydrofuran	55%

1,3-thiazole-2-carboxylic acid (14190-59-1) + N1-(1,2,3,4-tetrahydroacridin-9-yl)hexane-1,6-diamine (249290-17-3) → C23H28N4OS

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 12h;	55%

Upstream product

• 3034-53-5 2-bromo-1,3-thiazole 
• 124-38-9 carbon dioxide 
• 288-47-1 1,3-thiazole 
• 14527-42-5 thiazole-2-carboxylic acid ethyl ester 
• 7732-18-5 water 
• 1192365-76-6 C₄H₂NO₂S^(1-)*Li⁽¹⁺⁾ 
• 115-08-2 thiocarboxamide 

Downstream Products

• 16733-88-3 N-phenylthiazole-2-carboxamide 
• 16733-85-0 thiazole-2-carboxamide 
• 910476-38-9 C₁₂H₉N₃OS 
• 1174651-14-9 N-(3-bromo-4-(2-(pyrrolidin-1-yl)ethoxy)phenethyl)thiazole-2-carboxamide 
• 1266338-01-5 N-(4-(2-chlorobenzamido)-3-methoxyphenyl)thiazole-2-carboxamide 
• 1266338-23-1 N-(2-chloro-4-(picolinamido)phenyl)thiazole-2-carboxamide 
• 30216-57-0 1,3-thiazole-2-carbonyl chloride 
• 924289-21-4 N-(2-acetyl-5-methoxyphenyl)-2-thiazolecarboxamide 
• 923289-31-0 C₁₃H₁₁BrN₂O₃S 
• 923289-16-1 C₁₄H₁₄N₂O₃S 

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